WINTER IS HANDS down my favorite season for fashion because it gives me more to work with—layers, texture, and outerwear—which naturally makes outfits more interesting and puts a bigger focus on fit and proportion. I love building a look piece by piece: a beanie, a sweater, a jacket, the right shoes. Between testing new pieces, pulling looks for shoots, and wearing everything from early mornings to late nights, it’s when you see what really works—and what can handle an outfit repeat. Compared to summer, when getting dressed is pretty stripped down (literally) to the basics, winter gives you more room to play. You can mix tailored and casual pieces, bounce between relaxed and sharper fits, and switch things up without needing a new rotation of clothes.
That flexibility shows up across this season’s biggest men’s trends. They’re all rooted in familiar style territory—sportswear, Ivy League prep, ‘90s-inspired fits, and rugged outdoor gear—but updated with looser silhouettes, warmer color palettes, and pieces that make sense for everyday life. To narrow it down, we tapped menswear expert and stylist Ted Stafford to help pinpoint the winter trends worth paying attention to right now.
SportsCenter: Retro Athletic, Replayed
This trend pulls straight from vintage sports style, but polished enough for a coffee run or casual dinner. Expect fitness-inspired silhouettes like track jackets, snap-front pants and raglan-sleeve baseball tees that feel relaxed without looking sloppy. Color does a lot of the work here. Earthy tones like brown, burnt orange, mustard yellow, forest green, and creamy off-whites dominate, giving sporty pieces a warmer, more grown-up feel. Footwear anchors the look. Retro sneakers, especially slim, torpedo-style silhouettes, do the heavy lifting, instantly leveling up simple outfits like sweats and a jacket or jeans and a tee.
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Prepped Up: Ivy League, But Practical
Preppy is back, but it’s less country club, and more timeless. This is Ivy League style stripped of stiffness and rebuilt for everyday. The foundation is the usual suspects: crewneck and cable-knit sweaters, Oxford shirts, rugby shirts, neckties, tailored blazers, and cozy cardigans that layer without feeling bulky. Bottoms lean classic but comfortable, with corduroy pants and chinos replacing anything overly slim (skinny). Loafers are the must-have slip-on shoes, working with jeans and a sweater as they do with chinos and a blazer. Clean leather shoes also fit right in.
The New ’90s: Relaxed, Not Sloppy
The ’90s revival continues, but winter’s take is cleaner and more dialed in. It’s all about loosened silhouettes that still feel sharp. Straight-leg and relaxed pants lead the way, paired with easygoing tops like oversized crewnecks, vintage-inspired denim shirts, all layered under bomber jackets that sit just right on the shoulders. Everything has breathing room without being baggy, but proportions stay in check, which is what keeps it feeling current. The color palette sticks to neutral and versatile—black, navy, gray, olive, washed denim—making this an easy trend to plug into your existing wardrobe.
Country Man: Rugged, Weather-Ready Style
This is winter dressing at its most functional–built for cold mornings, unpredictable weather, and clothes that can take a beating. Even if the roughest terrain you face is a city sidewalk. The uniform starts with flannel shirts, thermal layers, and fleece jackets, topped off with puffer vests or heavier outerwear that’s made to last. Accessories matter here: field watches, sturdy belts, leather gloves, and cozy beanies. On the footwear front, work boots and hiking-inspired boots dominate—durable, grippy, and ready for whatever winter throws your way.
Meet the Expert
Ted Stafford brings over 20 years of experience in the fashion industry and has styled Men’s Health stories and covers for more than five years. His approach centers on timeless pieces, modern fits, and clothes that are wearable for everyday life.
More of Our Favorite Styles
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As the Style and Commerce Editor for Men’s Health, Joseph covers all-things fashion and grooming. Previously, Cheatham was a commerce editor for Spy, and he has written for Travel + Leisure.
Christian is the deputy commerce editor at Men’s Health and Women’s Health, where he oversees shopping content for both brands. He started his magazine career as an accessories assistant at Vogue, and has since held editorial roles at Tatler Asia and The Manual. When he’s not online shopping, you can find him on long walks with his two corgis.
